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Imipenem, Imipemide(former USAN), MK-0787, Tienam

亚胺培南(一水物) 亚胺培南 Chemical Name: [5R-[5alpha,6alpha(R*)]]-6-(1-Hydroxyethyl)-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.O]hept-2-ene-2-carboxylic acid monohydrate
CAS No. 74431-23-5, 64221-86-9 (anhydrous)
项目整合开发状态: Launched-1985
项目研究机构: Merck & Co. (Originator)
合成路线:By reaction of thienamycin (I) with methyl formimidate (II) by means of NaOH in water.
📌 参考资料/链接:
参考文献标题:Derivatives of thienamycin and its isomers
文献作者:Christensen,B.G.; et al.(Merck & Co.,Inc.)
参考来源:DE 2652679; FR 2332012; GB 1570990; NL 7612939

📄 详细内容


合成路线:By reaction of thienamycin (I) with methyl formimidate (II) by means of NaOH in water.

参考文献标题:MK-0787
文献作者:Serradell,M.N.; Castar,J.; Blancafort,P.
参考来源:Drugs Fut 1980,5(3),136


合成路线:The reaction of (3R,5R,6S)-6-(1(R)-hydroxyethyl)-2-oxo-1-carbapenem-3-carboxylic acid p-nitrobenzyl ester (I) with diphenyl chlorophosphate by (II) means of DMAP and DIEA in DMA/dichloromethane gives the enol phosphate (III),which is condensed with 2-aminoethanethiol (IV) in DMA to yield the 2-aminoethylsulfanyl derivative (V).The reaction of (V) with benzyl formimidate (VI) by means of DIEA in DMA affords the intermediate p-nitrobenzyl ester (VII),which is finally hydrogenated with H2 over Pd/C in water/isopropanol/N-methylmorpholine to provide the target Imipemide.

参考文献标题:Process for the preparation of imipenem
文献作者:Kumar,Y.; Tewari,N.; Rai,B.P.(Ranbaxy Laboratories Ltd.)
参考来源:WO 0294828


合成路线:The condensation of 7-oxo-6-(1-hydroxyethyl)-3-(diphenoxyphosphate)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid p-nitrophenyl ester (I) with the bis(trimethylsilyl) derivative of 2-(iminomethylamino)ethanethiol (II) in the presence of base gives p-nitrophenyl ester of MK-0787,protected with a trimethylsilyl group (III),which is finally deprotected by hydrogenolysis.
参考文献标题:A direct transformation of bicyclic keto esters to N-formimidoyl thienamycin
文献作者:Reamer,R.a.; Sletzinger,M.; Hartner,F.W.; Liu,T.; Shinkai,I.
参考来源:Tetrahedron Lett 1982,23(47),4903


产品链接: CAS No. 74431-23-5››

产品链接: CAS No.64221-86-9››